In September, the summer crowds disperse, the sun's intensity wanes, and it's a fantastic time to visit Annapolis and the Chesapeake Bay region. Enjoy historical sites and museums, crowd-free shopping and dining, and outdoor activities-whether hiking a trail at one of the area's parks or paddling on the water. Also, consider taking in the Maryland Renaissance Festival in Crownsville. With this 22-acre fictional 16-century English village with over 200 performers, ten stages, a 5,000-seat jousting arena, 148 craft shops and 48 food/beverage facilities, it's Maryland's premier outdoor event.

First Sunday Arts Festival
When: Sunday, September 2 (and every first Sunday through November) Noon to 5:00 p.m.
Where: First block of West and Calvert Streets, Annapolis
Admission: Free

Enjoy live entertainment and the works of 100 local and regional artists as you stroll along the first block of West Street and Calvert Street next to Whitmore parking garage. Local restaurants set up outside cafes that are perfect for people watching and an afternoon bite to eat. Free parking for the family-friendly event is available at the state parking garage on the corner of Calvert and Bladen Streets. Visit for more information.

Blowing Bubbles at the Renaissance Festival

Maryland Renaissance Festival
When: Weekends and Labor Day, August 26 through October 23; 10:00 a.m. – 7:00 p.m.
Where:1821 Crownsville Road, Annapolis

The region’s premier outdoor event and second largest Renaissance Festival in the country is celebrating its 41st season at Revel Grove. Travel back in time as you immerse yourself in the culture of a 16th-century English village, complete with King Henry VIII and his court. The festival includes 200+ entertainers, ten stages, a 3,000 seat jousting arena, 122 craft shops, 48 food and beverage emporiums, games, attractions and 85 acres of complimentary parking. Let merriment abound! Visit for more information.

Annual Maryland Seafood Festival
When: Saturday-Sunday, September 8-9; Saturday, 10:00 a.m. to 9:00 p.m.; Sunday, 10:00 a.m. to 7:00 p.m.
Where: Sandy Point State Park, 1100 East College Parkway, Annapolis
Admission: Adults, $15; kids 12 and under, free. Parking passes, VIP tickets and crab soup cook-off tickets are also available.

Highlights of this year’s festival include: the 28th Annual Crab Soup Cook-off featuring Annapolis area restaurateurs and chefs in a classic Maryland Showdown, cooking classes, mouth-watering food, entertainment by local and soon-to-be-discovered bands, kids’ activities and competitive beach volleyball for adults. Visit for more information.

Maryland Seafood Festival

Anne Arundel County Fair
When: Wednesday - Sunday, September 12 - 16
Where: Anne Arundel County Fairgrounds, 1450 Generals Highway, Crownsville

For nearly 65 years, the Anne Arundel County Fair has been amusing visitors of all ages with fun contests including hog calling and watermelon eating! Booths feature everything from homemade wine and home-brewed beer to furniture and one-of-a-kind Christmas decorations. Kids will enjoy the amusement rides, illusionist show, 4H Club animals and interactive car racing. There’s something for everyone! Visit for more information.

Anne Arundel County Fair

Blazers, Bourbon, Cigars
When: Thursday, September 28
Where: William Paca House and Garden, 186 Prince George Street
Admission: TBD

Enjoy an action-packed night of bourbon tastings, fine cigars, wonderful food, and networking with the “Who’s Who” of Annapolis gentlemen. Gentlemen already well-versed in the art of drawing subtle flavors out of a glass of aged whiskey and those just wanting to learn more will enjoy this unique evening featuring more than a dozen varieties of bourbon. VIPs enjoy early admission at 5:00 p.m. for a private tasting hosted by a master Maker’s Mark specialist, John Vicker-Smith II. He’ll describe current trends in bourbon while leading a deep sensory dive into the rich flavor profiles of different bourbons. VIP guests will enjoy all-you-can-taste bourbon with a special memento to take home, an exclusive Maker’s Mark cigar, and other surprises. Sponsored by: Maker’s Mark. Visit for more information.

Annual Boatyard Beach Bash
When: Saturday, September 15; 5:00 p.m. to 10:00 p.m.
Where: Annapolis Maritime Museum, 723 Second Street, Annapolis
Admission: General admission, $75 – includes dinner and 2 beverage vouchers; VIP (Very Important Parrotheads), $125 – ticket holders get to mingle with the band members and enjoy all the benefits of general admission.

Event founding sponsor, Boatyard Bar and Grill, has put together a star-studded lineup that includes original members of Jimmy Buffett’s Coral Reefers band performing on a waterfront stage. In 2017, Peter Mayer, Brendan Mayer and Doyle Grisham – as well as world-class musicians, John Frinzi, Scott Kirby, Aaron Scherz and Sunny Jim, along with James White and JD Spradlin from Radio Margaritaville, entertained throughout the evening. Evening includes an extensive grilled buffet dinner and cocktails. Proceeds benefit the Annapolis Maritime Museum’s children’s education efforts.

Greenstreet Gardens Fall Festival
When: September 22 - October 28; 10:30 a.m. to 5:00 p.m.
Where: Greenstreet Gardens, 391 West Bay Front Road, Lothian, MD 20711

Six weekends of fall festivities is back and even better than before! Come enjoy different themed events and activities each weekend with family and friends. Our 5-acre corn maze, pumpkin bowling, jumping pillow, haunted hay ride, cow train, giant teepee, corn box, straw castle, underground slide and more - is everything you could ever imagine!

MD Ave/State Circle Fall Festival

Dinner Under the Stars
When: Every Wednesday evening, through September 19th.
Where: The first block of West Street in downtown Annapolis
Admission: Making reservations ahead of time is highly recommended. 

The first block of West Street (from Church Circle to Calvert Street), located in the heart of the Arts District, will be closed to traffic on Wednesday evenings and filled with café tables reminiscent of the open air cafés in France, Spain, and Italy. Live music and special art exhibits will appear all over West Street, adding to the ambiance as you dine beneath a canopy of lights. 

Homestead Gardens Annual Fall Festival
When: Saturday, September 22; 11:00 am - 6:00 pm
Where: Homestead Gardens, 743 West Central Avenue, Davidsonville

Homestead Gardens' Annual Fall Festival is the largest in the area! Enjoy this family tradition featuring 15 rides and attractions, demonstrations, entertainment, food and beverages – including Homestead’s world famous apple cider doughnuts. New This year is the Midway and the Midway Bee Stage in the nursery where you will find special shows and music geared to families, the pumpkin express’s “cousin” the Bee Express, carnival games under the tent, sweet treats and more. In the lower field there is live music on the main stage, the pipe slide, straw maze for the little ones, corn holes, the new “human Bowling ,” delicious food and beverages at Homestead’s “Grab & Go,” and Kona Ice.

Homestead Gardens Fall Festival

Historic Hauntings Tours
When: Fridays & Saturdays & Holiday Weekend Sundays, September 7 - 29
Where: Tours depart from the Historic Annapolis Museum Store, 99 Main Street, Annapolis Admission: Adults, $22; Children ages 3-11, $14; Children 2 and under, free

This year, instead of heading to the usual haunted house full of unconvincing tricks, join Watermark on a special ghost tour of Annapolis with a costumed guide. Presented in concert with the Historic Annapolis Foundation, the tour will include the inside of a “spooky” historic house. Visit for more information.

Kunta Kinte Heritage Festival
When: September 29, 10:00 am – 7:00 pm
Where: Susan Campbell Park - Dock St, Annapolis
Admission: Free (Donations are greatly appreciated)

Enjoy the rich heritage of Kunta Kinte whose story from the Gambia to Annapolis and for generations on down was told in the book Roots: Saga of an American Family by Alex Haley.  A family-friendly cultural festival celebrating the history and Heritage of people of African American, African, and Caribbean descent. This is the 29th year of this celebration that includes a full day of live music, dance, ethnic foods and wares for sale. You can discover a full list of events and activities HERE.

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Additional September Links

  • Renaissance Festival

    Renaissance Festival

    One of Maryland's most anticipated events of the summer, the Renaissance Festival has a little something for everyone in the family.

    Learn more